If you’re a reasonable, rational-thinking human being, you may be wondering why anyone would risk developing carpal tunnel by handwriting 100 letters for a fast-food chain’s sweepstakes… and then post the process on the Internet.

Well here’s why I’m doing it.

Per the rules of McDonald’s annual Monopoly Game — and to comply with their “no purchase necessary” claim — participants are allowed to request game pieces by mail, as long as they send a handwritten, self-addressed, stamped envelope (“SASE” for short) to McDonald’s between certain dates (this year it’s September 18th and October 22nd, 2012).

If you fill out the envelopes correctly, Mickie D’s will mail your SASE back with 2 game pieces in it. Each game piece includes 2 game stamps, so altogether you get 4 game stamps for a combined 90 cents postage per letter, plus the cost of envelopes. In all, I should be receiving 400 game stamps from Ronald McDonald for a combined total cost of about $117.

Compare that to the cheapest eligible menu item, hash browns, which cost 99 cents a piece in south Florida and only net 2 game stamps. To collect an equivalent number of stamps, I’d have to buy over $200 in hash browns. If you checked our McDonald’s Monopoly Calculator, you’d see that it takes quite a few hash browns to have a shot at winning any of the top prizes. I’m not expecting to win anything big, but I want to better my chances while also minimizing my investment.

So that’s my first reason for writing the letters: It’s cheaper than buying McDonald’s food, and it actually nets more pieces than most eligible food items. Win/win.

But I’m not just gonna risk getting blisters to score some game stamps and hope to win a Fiat or something. My interest is deeper than that.

After a quick Internet search, I wasn’t able to come across anyone who’d attempted to send in this many letters, so I’m curious to see if McDonald’s will live up to their word and mail me 400 game stamps. Also, I’d like to see if I actually make a return on my money. It’s pretty hard to make any money back going the traditional route of buying a bunch of food, even the cheapo hash browns. So I’m curious to see if I can score more than $117 in prizes with my 400 game stamps.

Ok, so I’ve explained why I’m writing and mailing them, but why would I chronicle it? Well, why not? It’s the Internet, and it seems like a fun thing to do. Plus, like I said, I haven’t found anyone who’s sent in 100 letters and maybe, just maybe, this post will stop some poor fool years from now from repeating my calamity. So I’m really helping you guys, kind of.

I will be continually adding to this post to update my progress. So without further adieu, here’s a look into the process of handwriting 100 letters to McDonald’s.

Step 1: Mapping out everything I need

First, I made sure I took note of everything I’d need:

1. Request Envelopes: these will be the envelopes I send to McDonald’s requesting my pieces. It has to be handwritten and sent to their provided address.

2. Return Envelopes (SASE): This is the envelope McDonald’s will send back to me with pieces inside. So I’ll have to put it in my request envelope. Luckily, McDonald’s doesn’t say anything about writing a letter requesting pieces or anything — you just have to send this return envelope, handwritten of course.

3. Lots of stamps: I will need to buy 200 stamps total — 100 for the request envelopes and 100 for the return envelopes.

Step 2: Buying the supplies

I went to my local supply store and grabbed a box of 250 envelopes ($19.99) and two rolls of 100 postage stamps ($89). I bought two rolls of stamps because I need 100 stamps for mailing the request envelopes and another 100 stamps to put on my return envelopes.

Step 3: Back to the store (Fail #1)

Being the genius that I am, I didn’t take into account that I’d need smaller return envelopes to put inside the request envelope, so I went back and bought a box of 100 6 inch envelopes ($6.59) that fit inside the larger request envelopes.

Step 4: What am I writing?

I made sure to read the rules over a million times before I began my handwriting assault. Here is the provided McDonald’s mailing address:

This is what I will be writing verbatim 100 times on my request envelopes along with my return address in the top left. On the SASE envelopes all I need is to self-address it in the center and put postage. 100 times. No biggie.

So total I will be handwriting 100 request envelopes with McDonald’s address and my return address, and 100 self-addressed return SASE envelopes. Total I’m looking at over 17,800 handwritten characters. Ugh.

Next up,

Step 5: Let the writing begin!

Tune back in to Bargaineering to see the next installment of my Journey to handwrite 100 letters for McDonald’s Monopoly Pieces.

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